Methyl bromoacetate → HCID 13457778, compound

HRID 647450Notes

Reaction equation

HRID 647450 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>C1C=CC=CC=1.[Ag]=O>[CH3:23][O:22][C:20]([CH2:19][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1)=[O:21]

Participants

5

Reactant 2

HCID 60984Methyl bromoacetateHCID 13457777Benzyl azepane-3-carboxylate

Product 1

HCID 13457778HCID 13457778, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 1.46 g 3-benzyloxycarbonylperhydroazepine and 1.06 g methyl bromoacetate in 30 ml benzene add 1.06 g silver oxide. Stir the reaction in the dark for 24 hr., filter and concentrate the filtrate in vacuo. Dissolve the residue in HCl (pH 1.5) and wash the solution with ether. Make the aqueous phase to pH 12 and extract with ethyl acetate. Dry and concentrate the extracts to obtain 1-methoxycarbonylmethyl-3-benzyloxycarbonylperhydroazepine.

Workup

  1. customthe reaction in the dark for 24 hr
  2. filtration, filter
  3. concentrationconcentrate the filtrate in vacuo
  4. dissolutionDissolve the residue in HCl (pH 1.5)
  5. washwash the solution with ether
  6. extractionextract with ethyl acetate
  7. customDry
  8. concentrationconcentrate the extracts

Sources & evidence

ORD record
ord-bf57770ef9704aa58ae1aef6d718b3f3
Source dataset
uspto-grants-1983_10
Patent number
US04409146

Reaction notes

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